Weekend Reading: Ask Before Quitting

This article appears as part of Casey Weade's Weekend Reading for Retirees series. Every Friday, Casey highlights four hand-picked articles on trending retirement topics and delivers them straight to your email inbox. Get on the list here.
Weekend reading ask before quitting Weekend reading ask before quitting
Weekend Reading

If you’ve read my book, Job Optional, you know there is much more to consider beyond your finances when it comes to stepping away from full-time work.


Here, author Jonathan Clements emphasizes four important questions to ask yourself prior to entering retirement:

📌 How can I transform myself from a diligent saver to a happy spender? Learn how to find joy in leveraging the money you worked so hard for. Start with smaller purchases that bring disproportionate happiness per dollar, which can help shift a frugal mindset gradually.

📌 What will get me out of bed in the morning? Daydream about how you will spend your time. Create a wish list of activities that bring eudaimonic happiness, challenge, passion and a sense of purpose.

📌 Who are the friends I’ll see regularly? It’s important to proactively plan for maintaining friendships in retirement. Counting on family alone may not suffice, but volunteering, retirement communities or other organizations can offer opportunities for social interaction and new friendships.

📌 What will my future self think of the decisions I make today? Consider the long-term implications of your decisions and remain flexible. As circumstances and your mobility change during retirement, it's important to ensure housing suitability for older age and to avoid making irreversible financial commitments.

Whether you refer to it as being “Job Optional”, your “Second Act” or something else, retirement is a complete life shift, and should be planned for as such.